Cyanamide → N7,N7-Dimethyl-7,8-dihydro-6H-indeno[5,6-e][1,2,4]triazine-3,7-diamine 1-Oxide

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Reaction Conditions

Reaction Steps

A mixture of nitroaniline 110 (0.50 g, 2.3 mmol) and cyanamide (0.4 g, 9.0 mmol) were mixed together at 80° C., cHCl (5 mL) added dropwise and the mixture heated at 100° C. for 3 h. A further aliquot of cyanamide (0.4 g, 9.0 mmol) and cHCl (1 mL) was added and the mixture stirred at 100° C. for 1 h. The mixture was cooled to 50° C., 7.5 M NaOH solution added until the mixture was strongly basic and the mixture stirred at 100° C. for 3 h. The mixture was cooled, diluted with water (30 mL), filtered, washed with water (2×10 mL), and dried. The residue was filtered through a short plug of silica, eluting with 10% MeOH/DCM, and the solvent evaporated to give 1-oxide 111 (246 mg, 44%) as a yellow powder: mp (MeOH/DCM) 212-216° C.; 1H NMR [(CD3)2SO] δ 7.93 (s, 1H, H-9), 7.34 (s, 1H, H-5), 7.11 (br s, 2H, NH2), 3.03-3.18 (m, 3H, H-7, CH2), 2.79-2.89 (m, 2H, CH2), 2.22 [s, 6H, N(CH3)2]; 13C NMR [(CD3)2SO] δ 159.9, 152.0, 148.6, 140.5, 128.9, 120.0, 114.1, 67.0, 43.2 (2), 37.0, 36.1. Anal. calcd for C12H15N5O.½H2O: C, 56.7; H, 6.3; N, 27.5. Found: C, 56.9; H, 6.0; N, 27.4%.

Provenance & Evidence